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Issue 89, 2016
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Copper-catalyzed cascade cyclization of 1,5-enynes via consecutive trifluoromethylazidation/diazidation and click reaction: self-assembly of triazole fused isoindolines

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Abstract

Copper-catalyzed cascade cyclization of 1,5-enynes with two types of hypervalent reagents was developed via consecutive trifluoromethylazidation/diazidation and intramolecular click reaction (CUAAC), providing one-pot self-assembly of triazole fused isoindolines bearing a trifluoromethyl or an azide moiety. Moreover, the construction of a trifluoromethylcyclopropyl unit, which has been considered as a metabolically stable replacement for a tert-butyl moiety and was difficult to access, was also achieved under trifluoromethylazidation conditions. All these reactions exhibited excellent chemoselectivity, good to excellent yields and broad functional group tolerance.

Graphical abstract: Copper-catalyzed cascade cyclization of 1,5-enynes via consecutive trifluoromethylazidation/diazidation and click reaction: self-assembly of triazole fused isoindolines

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Publication details

The article was received on 10 Sep 2016, accepted on 17 Oct 2016 and first published on 17 Oct 2016


Article type: Communication
DOI: 10.1039/C6CC07394H
Citation: Chem. Commun., 2016,52, 13163-13166
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    Copper-catalyzed cascade cyclization of 1,5-enynes via consecutive trifluoromethylazidation/diazidation and click reaction: self-assembly of triazole fused isoindolines

    L. Yu, Y. Wei and M. Shi, Chem. Commun., 2016, 52, 13163
    DOI: 10.1039/C6CC07394H

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